US5902828A - Fungicidal mixtures - Google Patents

Fungicidal mixtures Download PDF

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Publication number
US5902828A
US5902828A US08/750,061 US75006196A US5902828A US 5902828 A US5902828 A US 5902828A US 75006196 A US75006196 A US 75006196A US 5902828 A US5902828 A US 5902828A
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US
United States
Prior art keywords
dithiocarbamate
formula
ethylenebis
compound
iic
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US08/750,061
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English (en)
Inventor
Eberhard Ammermann
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BASF SE
Original Assignee
Individual
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Publication date
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Assigned to BASF AKTINEGESELLSCHAFT reassignment BASF AKTINEGESELLSCHAFT ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: AMMERMANN, EBERHARD, HAMPEL, MANFRED, LORENZ, GISELA, MAPPES, DIETRICH, SCHELBERGER, KLAUS
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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
    • A01N37/50—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids the nitrogen atom being doubly bound to the carbon skeleton

Definitions

  • the present invention relates to a fungicidal mixture which comprises
  • the present invention also relates to methods for controlling harmful fungi using mixtures of compounds I and II and to the use of compounds I and compounds II for producing mixtures of this type.
  • the compounds of the formula I can have the E or Z configuration for the C ⁇ X double bond (relative to the carboxyl group). Accordingly, they can each be used either as pure E or Z isomer or as E/Z isomer mixture in the mixture according to the invention.
  • the E/Z isomer mixture or the E isomer is preferably used, and the E isomer is particularly preferred.
  • the pure active ingredients I and II are preferably employed in the preparation of the mixtures, which can as required be admixed with further active ingredients against harmful fungi or other pests such as insects, arachnids or nematodes, or else herbicidal or growth-regulating active ingredients or fertilizers.
  • mixtures of compounds I and II and simultaneous conjoint or separate use of the compounds I and II are distinguished by an excellent action against a wide range of phytopathogenic fungi, in particular from the class of Ascomycetes and Basidiomycetes. Some of them have systemic activity and can therefore also be used as foliar and soil fungicides.
  • Erysiphe graminis (powdery mildew) on cereals, Erysiphe cichoracearum and Sphaerotheca fuliginea on curcurbits, Podosphaera leucotricha on apples, Uncinula necator on vines, Puccinia species on cereals, Rhizoctonia species on cotton and lawns, Ustilago species on cereals and sugar cane, Venturia inaequalis (scab) on apples, Helminthosporium species on cereals, Septoria nodorum on wheat, Botrytis cinera (gray mold) on strawberries and vines, Cercospora arachidicola on peanuts, Pseudocercosporella herpotrichoides on wheat and barley, Pyricularia oryzae on rice, Phytophthora infestans on potatoes and tomatoes, Plasmopara viticola on vines, Alternaria species on
  • the compounds I and II can be applied simultaneously, conjointly or separately, or successively, and the sequence of separate application generally has no effect on the result of control.
  • the compounds I and II are normally used in a ratio by weight of from 50:1 to 2:1, preferably 40:1 to 1.8:1, in particular 30:1 to 1.8:1 (II:I).
  • the application rates of the mixtures according to the invention depend on the nature of the desired effect and are from 0.005 to 0.5 kg/ha, preferably 0.01 to 0.5 kg/ha, in particular 0.01 to 0.3 kg/ha, for compounds I.
  • the application rates for compounds II are correspondingly from 0.1 to 10 kg/ha, preferably 0.5 to 5 kg/ha, in particular 1 to 4 kg/ha.
  • the application rates of the mixture for seed treatment are generally from 0.001 to 100 g/kg of seeds, preferably 0.01 to 50 g/kg, in particular 0.01 to 10 g/kg.
  • the separate or conjoint application of the compounds I and II or of the mixtures of compounds I and II takes place by spraying or dusting the seeds, the plants or the soil before or after sowing the plants or before or after emergence of the plants.
  • the fungicidal synergistic mixtures according to the invention, or the compounds I and II can be prepared, for example, in the form of directly sprayable solutions, powders and suspensions or in the form of high-percentage aqueous, oily or other suspensions, dispersions, emulsions, oil dispersions, pastes, dusting agents, scattering agents or granules, and be used by spraying, atomizing, dusting, scattering or pouring.
  • the application form depends on the purpose of use; it should in every case ensure dispersion of the mixture according to the invention which is as fine and uniform as possible.
  • the formulations are produced in a conventional way, eg. by adding solvents and/or carriers.
  • Inert additives such as emulsifiers or dispersants are normally mixed with the formulations.
  • Suitable surface-active substances are the alkali metal, alkaline earth metal and ammonium salts of aromatic sulfonic acids, eg. lignin-, phenol-, naphthalene- and dibutylnaphthalenesulfonic acid, and of fatty acids, alkyl- and alkylarylsulfonates, alkyl, lauryl ether and fatty alcohol sulfates, and salts of sulfated hexa-, hepta- and octadecanols or fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and its derivatives with formaldehyde, condensation products of naphthalene or of naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ethers, ethoxylated isooctyl-, octyl- or nonylphenol, alkyl
  • Scattering and dusting powders can be produced by mixing or milling together the compounds I or II or the mixture of compounds I and II with a solid carrier.
  • Granules are normally produced by binding the active ingredient or ingredients on a solid carrier.
  • fillers and solid carriers which are used are mineral earths such as silica gel, silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground plastics, and fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products such as cereal flour, bark meal, wood meal and nutshell meal, cellulose powder or other solid carriers.
  • mineral earths such as silica gel, silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground plastics, and fertilizers such as ammonium sulfate, ammonium phosphate,
  • the formulations generally contain from 0.1 to 95% by weight, preferably 0.5 to 90% by weight, of one of the compounds I or II or the mixture of compounds I and II.
  • the active ingredients are employed for this,purpose in a purity of from 90% to 100%, preferably 95% to 100% (according to NMR or HPLC spectrum).
  • the compounds I or II or the mixtures or the corresponding formulations are used by treating the harmful fungi, or the plants, seeds, soil, areas, materials or rooms which are to be kept free of them with a fungicidally effective amount of the mixture or of the compounds I and II on separate application.
  • the use can take place before or after attack by the harmful fungi.
  • the active ingredients were prepared separately or conjointly as 20% strength emulsion in a mixture of 70% by weight of cyclohexanone, 20% by weight of Nekanil® LN (Lutensol® AP6, wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols) and 10% by weight of Emulphor® EL (Emulan® EL, emulsifier based on ethoxylated fatty alcohols) and diluted to the required concentration with water.
  • Nekanil® LN Litensol® AP6, wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols
  • Emulphor® EL Emulphor® EL
  • E efficacy to be expected expressed as % of untreated control on use of the mixture of active ingredients A and B in concentrations a and b
  • An efficacy of 0 means that the attack on the treated plants corresponds to that on the untreated control plants; an efficacy of 100 means that the treated plants show no attack.
  • Pot vines (variety: Muller Thurgau) were sprayed to run-off with the active ingredient preparation. After 8 days, the plants were sprayed with a suspension of zoospores of the fungus Plasmopara viticola and initially stored at 24° C. and 100% humidity for 48 h. The test plants were then left in a glasshouse at 20-30° C. for 5 days. Before the assessment, the plants were stored at high humidity for a further 16 h. The evaluation took place by inspection of the undersides of the leaves.
  • Leaves of tomato plants (variety: Gro ⁇ e Fleischtomate) were initially treated with the aqueous preparation of the active ingredients. After about 48 h, the plants were infected with a suspension of zoospores of Phytophthora infestans. The plants treated in this way were then incubated at 16-18° C. and a relative humidity of 100% for 6 days. The extent of fungal development was then determined.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Detergent Compositions (AREA)
US08/750,061 1994-06-10 1995-05-23 Fungicidal mixtures Expired - Lifetime US5902828A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE44202776 1994-06-10
DE4420277A DE4420277A1 (de) 1994-06-10 1994-06-10 Fungizide Mischungen
PCT/EP1995/001953 WO1995034205A1 (de) 1994-06-10 1995-05-23 Fungizide mischungen

Publications (1)

Publication Number Publication Date
US5902828A true US5902828A (en) 1999-05-11

Family

ID=6520249

Family Applications (1)

Application Number Title Priority Date Filing Date
US08/750,061 Expired - Lifetime US5902828A (en) 1994-06-10 1995-05-23 Fungicidal mixtures

Country Status (22)

Country Link
US (1) US5902828A (da)
EP (1) EP0765119B1 (da)
JP (1) JP3836506B2 (da)
KR (1) KR100404404B1 (da)
CN (1) CN1075350C (da)
AT (1) ATE173881T1 (da)
AU (1) AU685283B2 (da)
BR (1) BR9507975A (da)
CZ (1) CZ287204B6 (da)
DE (2) DE4420277A1 (da)
DK (1) DK0765119T3 (da)
ES (1) ES2124552T3 (da)
HU (1) HU221028B1 (da)
IL (1) IL113898A (da)
NZ (1) NZ287435A (da)
PL (1) PL181354B1 (da)
RU (1) RU2144291C1 (da)
SK (1) SK281656B6 (da)
TW (1) TW282392B (da)
UA (1) UA46734C2 (da)
WO (1) WO1995034205A1 (da)
ZA (1) ZA954765B (da)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002092538A2 (fr) * 2001-05-14 2002-11-21 Vladimir Ivanovich Chikov Procede pour augmenter le rendement des cultures agricoles

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1216897A (zh) * 1996-04-26 1999-05-19 巴斯福股份公司 杀真菌混合物
US6114378A (en) * 1996-04-26 2000-09-05 Basf Aktiengesellschaft Fungicide mixtures
DE102004049761A1 (de) * 2004-10-12 2006-04-13 Bayer Cropscience Ag Fungizide Wirkstoffkombinationen

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0254426A2 (en) * 1986-07-18 1988-01-27 Zeneca Limited Fungicides
US4829085A (en) * 1986-07-16 1989-05-09 Basf Aktiengesellschaft Oxime ethers and fungicides containing these compounds
GB2267644A (en) * 1992-06-10 1993-12-15 Schering Ag Mixed class synergistic fungicide based on pyrimethanil
GB2279568A (en) * 1993-07-02 1995-01-11 Ciba Geigy Ag Synergistic microbicide composition for plants
CA2131854A1 (en) * 1993-09-24 1995-03-25 Horst Wingert Fungicidal mixtures
WO1995015083A1 (fr) * 1993-12-02 1995-06-08 Sumitomo Chemical Company, Limited Composition bactericide

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4829085A (en) * 1986-07-16 1989-05-09 Basf Aktiengesellschaft Oxime ethers and fungicides containing these compounds
EP0254426A2 (en) * 1986-07-18 1988-01-27 Zeneca Limited Fungicides
GB2267644A (en) * 1992-06-10 1993-12-15 Schering Ag Mixed class synergistic fungicide based on pyrimethanil
GB2279568A (en) * 1993-07-02 1995-01-11 Ciba Geigy Ag Synergistic microbicide composition for plants
CA2131854A1 (en) * 1993-09-24 1995-03-25 Horst Wingert Fungicidal mixtures
WO1995015083A1 (fr) * 1993-12-02 1995-06-08 Sumitomo Chemical Company, Limited Composition bactericide
EP0741970A1 (en) * 1993-12-02 1996-11-13 Sumitomo Chemical Company Limited Bactericidal composition

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
Chem. Abst. vol. 118, No. 23, Jun. 7, 1993, Abstract No. 228112. *
Research Disclosure Nr. 338, 1992 Havant GB, Disclosed Anonymously, Disclosure 33892, Mixtures of Fungicides and Insectcides. *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002092538A2 (fr) * 2001-05-14 2002-11-21 Vladimir Ivanovich Chikov Procede pour augmenter le rendement des cultures agricoles
WO2002092538A3 (fr) * 2001-05-14 2003-05-08 Vladimir Ivanovich Chikov Procede pour augmenter le rendement des cultures agricoles

Also Published As

Publication number Publication date
WO1995034205A1 (de) 1995-12-21
CN1075350C (zh) 2001-11-28
AU2615595A (en) 1996-01-05
SK281656B6 (sk) 2001-06-11
DK0765119T3 (da) 1999-08-16
HUT76143A (en) 1997-07-28
DE59504426D1 (de) 1999-01-14
PL317533A1 (en) 1997-04-14
CZ287204B6 (en) 2000-10-11
AU685283B2 (en) 1998-01-15
HU9603399D0 (en) 1997-02-28
TW282392B (da) 1996-08-01
HU221028B1 (hu) 2002-07-29
SK155896A3 (en) 1997-09-10
ES2124552T3 (es) 1999-02-01
IL113898A0 (en) 1995-08-31
ATE173881T1 (de) 1998-12-15
RU2144291C1 (ru) 2000-01-20
DE4420277A1 (de) 1995-12-14
ZA954765B (en) 1996-12-09
NZ287435A (en) 1997-11-24
EP0765119A1 (de) 1997-04-02
BR9507975A (pt) 1997-08-12
CZ355096A3 (en) 1997-05-14
PL181354B1 (pl) 2001-07-31
CN1150380A (zh) 1997-05-21
KR100404404B1 (ko) 2004-02-18
JP3836506B2 (ja) 2006-10-25
EP0765119B1 (de) 1998-12-02
IL113898A (en) 2000-02-17
UA46734C2 (uk) 2002-06-17
JPH10501247A (ja) 1998-02-03

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